- Cross-coupling reaction of organoalane reagents with 2-mercaptobenzo-5-membered heterocycles for efficient synthesis of benzo-5-membered heterocycle sulfides
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A highly efficient and simple route for the synthesis of benzo-5-membered heterocycles sulfides has been developed by the cross-coupling reaction of 2-mercaptobenzo-5-membered heterocycles with (hetero)arylaluminum reagents. Various benzo-5-membered heter
- Luo, Rui-Qiang,Guo, Shao Peng,Xiao, Hong-Liu,Li, Qing-Han
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- Selective C-H chalcogenation of thiazoles: Via thiazol-2-yl-phosphonium salts
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Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2-H chalco
- Zi, You,Wagner, Konrad,Sch?mberg, Fritz,Vilotijevic, Ivan
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p. 5183 - 5191
(2020/07/23)
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- Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes
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The thioetherification of heteroaryl chlorides is an essential synthetic methodology that provides access to bioactive drugs and agrochemicals. Due to their (actual or potential) industrial importance, the development of efficient and low-temperature protocols for accessing these compounds is a requirement for economic and ecologic reasons. A particular highly effective catalytic protocol using the Pd/PTABS system at only 50 °C was developed accordingly. The coupling between chloroheteroarenes and a variety of less reactive arylthiols and alkylthiols was carried out with a high efficiency. Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.
- Bandaru, Siva Sankar Murthy,Bhilare, Shatrughn,Cardozo, Jesvita,Chrysochos, Nicolas,Schulzke, Carola,Sanghvi, Yogesh S.,Gunturu, Krishna Chaitanya,Kapdi, Anant R.
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p. 8921 - 8940
(2019/07/08)
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- Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
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An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.
- Liu, Xing,Zhang, Shi-Bo,Zhu, Hui,Dong, Zhi-Bing
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p. 11703 - 11711
(2018/10/02)
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- Copper-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2- a ]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids
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An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2- a ]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2- a ]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived lung, stomach, esophageal, and breast cancer cell lines.
- Guo, Tao,Wei, Xu-Ning,Zhu, Ying-Li,Chen, Huan,Han, Shu-Lei,Ma, Yong-Cheng
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supporting information
p. 1530 - 1536
(2018/05/25)
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- Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature
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Inexpensive copper catalysts enabled direct C-H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C-S and C-Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited high catalytic efficacy even at a reaction temperature of 25 °C.
- Gandeepan, Parthasarathy,Mo, Jiayu,Ackermann, Lutz
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supporting information
p. 5906 - 5909
(2017/07/11)
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- New Synthesis and Biological Evaluation of Benzothiazole Derivates as Antifungal Agents
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In search of new antifungal agrochemicals that could replace commercially available, aryl-2-mercaptobenzothiazoles were synthesized. They were prepared by two methodologies, using both photostimulated reaction and microwave assisted reaction. These reactions took place without the use of metallic catalyst by a one-pot procedure with excellent yields (70-98%). Synthesized compounds were evaluated for fungal growth inhibition against Botrytis cinerea. Most of the compounds have an excellent antifungal activity, and three of these showed a superior inhibitory effect to commercial fungicide Triadimefon. IC50 values observed for 2-(phenylthio)benzothiazole, 2-(2-chlorophenylthio)benzothiazole, and 2-(3-chlorophenyl thio)benzothiazole were 0.75, 0.69, and 0.65 μg mL-1, respectively.
- Cano, Natividad Herrera,Ballari, María S.,López, Abel G.,Santiago, Ana N.
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p. 3681 - 3686
(2015/04/27)
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- Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole
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A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 °C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 °C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively.
- Li, Xiaokang,Yuan, Tangjun,Yang, Yu,Chen, Junmin
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supporting information
p. 9652 - 9660
(2015/01/09)
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- The direct thiolation of benzothiazole catalyzed by copper complex in superbase system
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The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields. Georg Thieme Verlag KG Stu
- Wang, Xiaowei,Li, Yanjun,Yuan, Yu
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p. 1247 - 1255
(2013/06/04)
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